


Your Last Hurrahs with Dean!

by AmeliaSPN1973



Category: Supernatural
Genre: #not a fix it fic, Birthday, Bunker Life, Death, F/M, Love, Major character death - Freeform, Not Beta Read, Porn With Plot, Romance, Smut, Violence, carry on, happiness, insert reader - Freeform, season 15 spoilers
Language: English
Status: In-Progress
Published: 2021-01-18
Updated: 2021-01-18
Packaged: 2021-03-17 05:02:32
Rating: Explicit
Warnings: Major Character Death
Chapters: 4
Words: 7,149
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28843542
Author URL: https://archiveofourown.org/users/AmeliaSPN1973/pseuds/AmeliaSPN1973
Summary: You and Dean go back over ten years, but haven’t seen each other in 3-4 years. What happens when he comes back to see you one last time before Chuck destroys the world.
Relationships: Dean Winchester x Reader, Dean Winchester x You, Dean Winchester/Reader, Dean Winchester/You
Comments: 1
Kudos: 6





	1. Chapter 1

It was mid morning on Saturday as you began to open your eyes, but immediately regret the decision when you feel the pounding behind them. “Ugh!” You grunted, closing your eyes again. This seemed to appease the hangover gods. You breathed a few times and began to feel around you. You felt the fitted sheet under you, the flat sheet and light quilt over you. You then realized what you didn’t feel were the pajamas you normally wear; you were completely naked. Slowly opening your eyes again, dealing with the throbbing in your head, you got up, putting on your robe, and padded to the bathroom. After doing your business, you walked out of your room towards the kitchen searching out coffee. As you passed your living room, you turned your head to the side to see him sprawled out on his stomach sleeping on the couch. Dressed only in his boxer briefs, Dean Winchester was absolutely gorgeous with his light brown hair, strong jaw bone, beautiful eye lashes and pouty lips, not to mention his beautiful back muscles, strong thighs, bow legs, and taut buttocks. You immediately recalled last night’s events in your mind. 


	2. The night before

Eleven Hours Earlier...

It was your XX birthday on (Y/BD) and your friends convinced you to go out with them to the local bar, the Wayward Pub. The party started at seven and for the next two hours, you spent most of your time at a table with a sign your friends made that said, _ I’m Y/N and it’s my birthday so buy me a Margarita. If I’m thankful, you just might get a kiss _ . You scolded your friends on the sign. “I’m not going to take drinks from strange men or even men I know and kiss them just because they give me a drink,” but your friends laughed at you. “Just enjoy the attention.”

It was nine at night when the door opened and everything changed. In a three piece suit, looking like a GQ model, he walked in and looked around the bar. As soon as your eyes met, they locked and your breath hitched. You watched as his tongue slipped out to wet his lips which caused your tongue to do the same, wishing it was his tongue that was wetting yours. He was absolutely gorgeous. As soon as he walked up to the bar, you tried to distract yourself and watch your friends sing karaoke. It must have worked because you were soon startled by a voice. “I hear it’s your birthday.” You looked up to stare into the beautiful olive green eyes of the incredibly handsome man with a margarita in his hand. “I was told you like margaritas.”

You immediately gave a big, warm smile. Standing in front of you was Dean Winchester, whom you hadn’t seen much of in four years now. You knew Dean and Sam Winchester for over a decade. You knew they hunted monsters, demons, and angels, as they saved you from a Vampire nest many years ago, killing your entire family and boyfriend at the time, Matt. Since you didn’t have any other family Dean and Sam took you under their wings for protection. At first they stayed with you when not staying at Bobby’s house or one of his cabins, but once they found the bunker, you moved there with them. You had a crush on Dean from the beginning but especially during those years living together in the bunker, you two grew close; however, you stayed friends, your relationship never becoming sexual, not that you didn’t want it to be. You cared a lot about Dean. He was strong, funny, loyal, smart and of course gorgeous, but he told you that he wasn’t good for you. While he thought he was a bad guy, you knew he truly a good guy. After seven years of friendship and living together, one night you got into a pretty heated argument with him over your “relationship”, so you left the safety of the bunker, returning back home to your empty house. You were completely heartbroken for both the friendship and what could have been. You ran into Dean the next year when he was on another hunt near your town. He stayed at your house which allowed you to talk things over, deciding you still wanted to remain friends. Since then, you became text and phone buddies, occasionally seeing each other, but still nothing sexual ever happened as he realized you were the one woman in his life he could be completely open and honest with; therefore he wouldn’t sleep with you. You weren’t exactly happy with your role in his life, but you accepted it. You looked at him in shock. “Dean! What are you doing here?”

“Well, it’s your birthday and I was passing through.” He set the drink down in front of you and smiled. You got up as he walked over and hugged you; he was warm and comforting; you noticed how your bodies still fit together perfectly. You inhaled deeply, smelling his musk and craving more contact as his hand rubbed circles along your back. However, you finally pulled away first, almost falling backwards, but he caught you with his strong arm around your waist, keeping you upright and against him. 

“You OK sweetheart?”

“I’m good.You know me. Clumsy as usual.” You felt him inhaling your scent from your neck and swore he kissed the top of your head before letting you go. He smiled as you sat down and took a long draw on the straw. The alcohol hit you quickly as you had not eaten much all day; your friends wanted to see how drunk you could get on an empty stomach. “Thanks.”

“You’re welcome. May I join you?”

“Of course.” You smiled, already feeling the effects of the alcohol and Dean’s warmth from before. 

He sat down next to you and you both began to talk. “Where have you been Winchester?”

“All over. You?”

“Here. Always here.” You both take a drink. “How’s Sam?”

“He’s good. He’s back at the bunker. He sends his love and birthday wishes.”

“Thanks. Yeah. He called me earlier and wished me a happy birthday. I wish he could have come too, but Eileen was back.” You looked at him curiously. 

“Yeah.” Dean moved in toward your ear and lowered his voice to a whisper. “We found a spell that can bring back the dead. I’m glad he has her.” He smiled. 

You smiled back. “That’s great Dean. I miss him too. So, you’re still at the bunker?”

“Yeah, we still live in the bunker.”

“Wow! I would have thought you’d have destroyed it by now.”

Dean laughed. “We almost did about two years ago, but it’s still standing. Sometimes I surprise myself.”

“And How’s Baby?”

“She’s still running, parked outside. She’s still one of my favorite girls.” You laughed and then internally frowned, thinking the car meant more to him than you did. You then brushed it off. “How have you been doing?”

“Living the dream as always.” He smiled his thousand watt smile with all the thousands emotions and meanings hidden behind his beautiful olive green eyes. 

“Aren’t we all.” You smile and your smile doesn’t match your eyes either. 

“Touché.”

Time ticked away, as you two made small talk until your friends, Denise and Kendra, finally walked over. “Hey Y/N. Who’s your friend?” Denise smiled, smitten by the handsome man.

“Denise and Kendra, this is Dean; he’s an old friend of mine. We’ve known each other over ten years.” You smiled.

“I’ve known this sweetheart for a long time. Probably the only woman I’ve had this long of a friendship with.” Dean smiled over at you. 

You pursed your lips. “I guess as friends, it’s easier to keep a relationship. Sex complicates things.” You replied with a bit more cynicism than you wanted to. You always hated yourself for not being the woman Dean wanted to be with. 

Dean looked over at you and saw your pout. He knew you always wanted more with him. He reached over, taking your hand and picking his words out carefully. “I don’t deserve a woman like you, one that sticks by me through all my shit and still cares for me. You really deserve so much more.”

Your friends looked at the two of you; the awkwardness and sexual tension was palpable. Denise smiled. “Well, I’m glad you two are reconnecting. It was nice to meet you Dean. We’re going to go back and do more Karaoke.” Kendra also smiled and they walked back to the karaoke stage.

“You know, they’re right. It’s good we’re reconnecting.” Dean smiled.

“Yeah.” You took another large drink from your glass.

One margarita turned into two, then three, four, and by five, all from Dean, and you were pretty hammered by then. As the evening progressed, you both moved in closer. 

You stared at each other, wishing for more time with him, yet anxious due to the closeness. Everytime you get close to him, he tells you how good a friend you are; the possible rejection becomes harder and harder to take each time. You needed to step away. “I think I might just sing a tune.” You smiled, got up, and began to sway back and forth as you walked towards the karaoke stage. You thought you were being sexy, but you just looked really drunk which made Dean chuckle. 

You let your friends finish their song, then got on stage. “This one is for all the ladies who have men who you would do everything for and want them to do everything to you, yet you’re friend zoned.” You looked right at Dean as the music to “I want you to want me” by Cheap Trick began to play. “I want you to want me. I need you to need me. I love you to love me. I'm begging you to beg me.” You belted out the song like you wanted the heavens to hear you, staring at Dean the entire time. You swayed your hips to the music, dancing more provocative than you ever had before. 

You watched Dean walk up to your friends and talk to them, all while keeping his focus directly on you. You watched them talking with Dean nodding. He smirked as Denise leaned in and whispered something to him. A twinge of jealousy hit you. You cared for him so much that it embarrassed you to be envious of your friend. You tried to stay focused on the song. 

After you finished that song, you sang Kiss me Slowly by Parachute. 

“Stay with me, baby stay with me,

Tonight don't leave me alone.

Walk with me, come and walk with me,

To the edge of all we've ever known.

I can see you there with the city lights

Fourteenth floor, pale [green] eyes.

I can breathe you in.

Two shadows standing by the bedroom door,

No, I could not want you more than I did right then,

As our heads leaned in.

Well, I'm not sure what this is gonna be,

But with my eyes closed all I see

Is the skyline, through the window,

The moon above you and the streets below.

Hold my breath as you're moving in,

Taste your lips and feel your skin.

When the time comes, baby don't run, just kiss me slowly.”

You moved your hips seductively to the song. Once done, you looked down at Dean who had moved to the stage and was looking at you with what looked like love or what you hoped would look like. . 

You stepped down off the stage and wobbled, teetering on falling. Dean reached his arm around your waist, pulling you flush against him to keep you upright.

Both your breaths were shallow as you stared into each other’s eyes. “Thanks.” You smiled.

“You’re welcome.” He smiled. You leaned over and kissed his cheek and pulled away quickly, smiling and looking down embarrassed. “Sorry.”

Dean smiled, cupping your chin in his hand, staring into your eyes. His hand moved up slowly placing it against your cheek as his lips moved in and pressed to yours. You immediately began to move your lips slowly with his, feeling his tongue sweep across your lips for access. Opening your mouth, you let his tongue meet yours in a tender kiss, much like the song you just sang. After the first kiss, he smiled, then kissed you again with more need, as you threw your arms around his neck, and began carding his hair. When you pulled away gasping for air, he waited as you both caught your breaths, then pressed both his hands to your face and kissed you again with more passion than you ever felt with anyone. You were lost in his lips. No one else was in the room, just you and him. It became sloppy and needy as your hands ran up and down his chest and back, while his hands moved up and down your torso. You gripped his shoulder blades, while he sucked on your tongue; you felt he was suffocating you, but you didn’t care; you could die in his arms, suffocating and choking on his tongue. You finally pulled away feeling drunk and horny which embarrassed you. Your arousal had soaked through your panties and you were concerned you were going to drip on the floor. You looked around to see everyone in the bar staring at you two, turning your cheeks bright red. “I need to use the restroom.” 

“OK Sweetheart.” Dean looked at you, judging how you were feeling from the kiss. You turn away walking towards the restrooms. 

Making it to the restroom, you did your business, then looked at yourself in the mirror. You looked happy; your face was flush as pink crept across your cheeks; your lips felt swollen from his kiss; and you felt really giddy. You were usually more melancholy and a sleepy drunk, but Dean made you smile. You splashed cold water on your face to sober up and cool down then reapplied the translucent pressed powder and lipstick. As you opened the bathroom door, Dean was standing there. “Hey sweetheart. Everything OK?”

Need came over you as you grabbed the collar of his suit jacket pulling him in the bathroom, throwing your arms around his neck and smothering your mouth to his. Your tongue sweeped the inside of his mouth tasting the whiskey and beer on his tongue. “I want you so bad. I need you Dean.” You continued kissing him, running your hands up and down his torso and then up through his hair. “I just want you to fuck me against this wall. Please. Don’t say ‘no’ or ‘we’re just friends’. Do this as a birthday present for me. You don’t have to say you love me. It can just be pure sex. I promise.” You smashed your lips against his in an even sloppier kiss. 

Dean turned locking the bathroom door, then pushed you back against the wall; his hands squeezing your buttocks as he pressed his bulge into you. 

Sliding your hands down Dean’s chest, you undid his belt then began undoing the zipper of his suit pants. You were desperate and needy. “Fuck! I need you.” 

Dean continued to kiss you as you began to palm the beginning of his bulge. You felt him growing harder against the palm of your hand. Finally, he pulled away, taking a step back. “I can’t. I don’t think you want to do this Y/N.”

“Yes. I do.” You slowly began pulling your dress up your thighs, slowly pushing the fabric above your waist, continuing up your torso palming your breasts as you pushed your dress up until it hung around your neck, leaving you in your silky black bra and panties. Your breasts were spilling out of the cups of your bra and your panties and inner thigh were wet in arousal. 

Dean bit his lip in admiration. “Fuck! You’re beautiful.”

You smiled. “So are you.” He moved in closer, staring into your eyes. He tucked a piece of hair behind your ear and placed a palm to your cheek. His other hand went to your waist, causing your skin to heat. You exhaled and breathily spoke. “Please Dean.” 

He slowly moved his hand up, inching slowly. His hand felt like searing heat as it trailed up your side. He watched your breath hitch and your stomach quiver until his hand gently cupped your breast, his thumb circling around the nipple; the dilemma of continuing raging in his head. 

“Yes please.” Your voice was raspy, laced in sex; your heart beating rapidly. 

Dean smiled watching and feeling the nub hardening as his thumb continued to circle and sweep across. He watched your breathing as you sucked in air sharply then released quickly, your breast heaving against his palm. He moved his hand up to press against your other cheek as his other hand moved down to your other breast, repeating the process, leaving a trail of heat down your other side. 

“Please.”

Grabbing your thighs, he hoisted you up. Quickly wrapping your arms around his neck and legs around his waist, he began humping you slowly, his breathing was as ragged as yours. You moaned, feeling his cloth covered erection hit your cloth covered clit. “Yes Dean. More.” He started thrusting harder, your covered barriers getting soaked in your arousals.

“Please Dee...please.”

He continued. You both were getting close. 

“Fuck me.” You were quietly chanting. “Fuck me. Fuck me.”

He finally stopped, exhaled, and looked at you sweetly. He pressed his hand to your cheek. “Sweetheart. I don’t think you will be happy with yourself if we fuck against the wall of this bathroom.” 

You pushed him away frustrated. “Of course. I get it. You don’t want me.”

“That’s not what I said, Y/N.”

“Then why don’t you want to fuck me?” This was always how your arguments started. You say you want him and he says he’s no good for you. You question why and he says you’re too good of a person and too good of friends. You feel the rejection, get hurt, and one of you leaves.

“Darling, you’re drunk and from our time together, I know this is not something you would normally do.”

“I want to be different than I normally am. I want to do this. It’s my birthday and I want to do this with you.” You reached your hand down the waistband of his slacks and boxers, grabbing his cock, feeling him expand in your hand as you began to stroke him. His cock twitched against you, his hips thrusting forward. “I want you in me Dean.” He moved his hand down over your hand as his other hand slipped behind your head and he pulled you to him in a blazing kiss. You felt him thrusting against your hands. Over and over, he got closer as your kiss continued. He finally grabbed your hand, pulling it from his crotch. “I do want to do this with you, Y/N, but not here. Let’s go to your place.”

One more kiss, then he helped you pull your dress down, grabbed your hand, and left the bathroom. You pull away from Dean, walking up to your friends to say your goodbyes. “Be safe,” Kendra smiled.

Denise took you to the side. “Are you OK going with him?” Denise looked concerned. “You told me about this guy when you moved back here years ago. You want to do this?” She was concerned. You were heartbroken the last time you left Dean, and she was looking out for you. 

“Yeah. I really do.” You smiled. “You know how I feel about him.”

“Please be safe. Call me tomorrow, OK?”

“I’ll call you when I can. I promise.” You look over to see Dean had his jacket draped over his arm in front of him, covering his erection and you realized your effect on him. You hugged your friends, smiled, then wobbled over to Dean. He put his arm around your waist, helping you out the door, and over to his car. 

“Hey Baby. Long time, no see.” You smiled while greeting the beautiful black 1967 Chevy Impala. You pulled Dean to you for another kiss while being pressed your against the door; your desire was getting the best of you; you both began pawing each other, feeling your bodies. Dean finally pulls away. “Let’s get you home.” He opens the door for you, and you grin at his gentlemanly gesture. You slid in, feeling the worn, soft leather underneath you. You loved that car when Dean would take you places in it or let you tag along on hunts. You always wanted to be with Dean in that car and one day, you will hopefully get that wish. 

Dean remembered where you lived and drove quickly. As soon as he pulled into your garage and parked the car, you immediately straddled his waist. “Please Dean.”

“So needy.” He smiled as you scraped your teeth against his lower lip. “Only for you.” 

You kissed, both your arousals soaking through your clothes. You ripped his belt out, tossing it to the backseat, unbuttoning, and unzipping the fly. Your hand reached down again and grasped his cock, while his hand slipped under your dress; his thumb applied pressure to your cloth covered clit. “Ah,” you moaned as he continued circling around that sensitive area. He moved his fingers down, slipping under your panties, as he invaded you slowly. Grinding your hips, he fucked you with his fingers as you fucked him with your hand. 

“Damn. I’m getting close, sweetheart.”

“Me too.” You were rolling your hips back and forth faster and harder as his fingers worked their magic on you. Finally arching your back, you came with a wail, as he grunted and released in your hand. Pulling your hand out, bringing it to your mouth, you licked off his cum as he brought his fingers to his mouth and sucked off your juices. 

Dean smiled and kissed you passionately as you tasted each other on your tongues. Getting out of his car, he grabbed your thighs as you wrapped around him and he carried you through the door. Setting you on your floor, you quickly worked your way back to your bedroom kissing and removing each other’s clothing, leaving a trail along the way. 

~~~~~~~~

As you lay back in your bed in your lace bra and panties and Dean in his boxer briefs, you sighed. “I need you in me so much Dean.”

“I got you.” Dean hovers above you as your lips continue to meet. Slowly he began moving down your jaw to the crease of your neck as you wrapped your legs around his waist, arms around his neck, feeling his weight above you. His lips moved down your chest, his tongue licking the salt and sweat between your cleavage. “You taste amazing.”

“It only took you ten years to realize this Winchester.”

He looked at you, irises lust blown. “I know.”

His tongue did another sweep as his hand reached around undoing your bra clasp. As the cups pulled away from your breasts, his lips puckered over the nipple as his tongue licked the nub.

A moan escaped your mouth and Dean did it again. “I love how you respond to me.”

“Yes.” You pressed your breasts to him, feeling him lap at the hardened pebble.

He helped remove your bra and began kissing down your stomach. Reaching your pantyline he looks up. “You sure?”

“Yes. Oh God yes. Please.”

Slipping his finger slowly into your waistband, he pulled them down slowly, his hands and lips committing your body and curves to memory. Once he got them off, he began kissing up your legs, between sides. You writhed happily, little sparks of electricity with each touch and kiss of his lips went straight to your core making you wet with desire, longing for him to be inside you. 

He continued slowly touching and kissing up the insides of your legs, to your inner thighs when the alcohol got the best of you and you finally passed out. 


	3. Reconnecting

As you stared at Dean on the sofa, you remembered why you were naked when you awoke. You remembered his lips, touch, and the heat between you. The fact that he had slept in the living room to protect your honor made you want him even more. You leaned over the sleeping man, reaching down, touching his shoulder, rubbing gentle circles. “Dean.”

Dean jumped up, yanking his knife from under the pillow, and pointing it at you. 

“Good morning?” You smiled. The tie had loosened on your robe, revealing some of your nakedness.

He looked at you, eyes focusing, until his eyes gazed up and down your body then met yours. “Y/N?”

“That’s me. Thanks for taking me home last night.”

“You’re welcome.” He licked his lips as he noticed a nipple had slipped out of your robe.

You remembered the kissing, the desire in the bathroom of the bar; how you got each other off in the car, and the replay in your bedroom, his lips against your breasts and your naked skin, moving up your legs, but you weren’t sure what else. “I don’t remember much after you drove me home; did we?”

“No. You passed out just as things were getting good.” He seemed disappointed. 

“Oh.” You were too. You rubbed your thighs together, still turned on by him. You looked down embarrassed and eyed up his body, seeing his morning erection. You licked your lips, as the blush rushed to your face. “I’m sorry Dean. I tried everything to seduce you last night. I know we have only been friends all these years but I’ve always cared about you as more than that. The alcohol really blurred the lines last night and for that I am truly sorry.”

Dean looked at you. He contemplated for a long pause, then spoke. “Truth is I’ve always liked you Y/N, but to keep you protected, I made sure I only kept you at a friend’s length, but something last night changed everything.” He moved closer to you. “I wanted you, I mean I really wanted you, but I would never take advantage of you and you weren’t fully lucid last night.” Tucking a stray hair behind your ear, he smiled. 

You stared at each other; both your hearts were racing. Finally he moved forward catching your face in his palms, kissing you passionately. He reached around your waist pulling you flush against him, his erection pressed against your stomach. Feeling him against you, you weren’t about to let the moment slip away. “Be with me Dean.”

“I will sweetheart. I will.” Lips and teeth smashed against each other. You licked his lower lip until he let you in, your tongue sweeping the inside of his mouth and meeting his. 

He grabbed your thighs lifting up as you wrapped your arms around his neck and your legs around his waist. Walking down the hall, pressing you against the wall so he could deepen the kiss, he finally made it to your bedroom and laid you down, crawling in after you. 

You spread your legs, letting him cradle between them as he pressed you into the mattress, and you continue to kiss. Running your hands up and down his torso, you felt his pecs, his stomach muscles rippling, moving around to the curve of his spine, his strong back and shoulder muscles, down around his round glutes. His lips moved down your jaw to the crease of your neck while his hand reached down pulling the tie of your robe. Slipping his hand under your robe, his hand left a blazing trail of heat as he moved up to your breast to squeeze. “Fuck! You have amazing breasts.”

Moaning, you arched into his hand. His lips puckered around the nipple as his tongue teased the nub. You arousal pooled below with each little nip and pucker of his lips. He moved to your other breast, giving it attention next then slowly moved down your torso around your hips to your inner thighs where he nipped and kissed between sides as you got wetter. 

“Damn Babe. All this is for me.” His hand swept up your pussy lips, sinking a digit in, working it in slowly until he found your g-spot, a rush of arousal came with it. 

“Yes Dean!” Your hips moved up, meeting his fingers, his tongue then lapped at your clit, then his mouth latched onto it and sucked. “Fuck yes! Please!” Writhing against his mouth, he continued working you over as your hand carded his hair. You cried out “please” like a chant until your eyes flashed white and you came with a flood of arousal. Pulling his fingers from you, he raised them to his mouth, pulling them in, and licking off your juices. “You taste amazing.”

Kissing back up your body, his lips met yours as you tasted yourself on your tongue. “Why did it take us this long?” Dean looked down at you tenderly. 

“Because you were an idiot, Winchester.” Your chiding him made him smile. 

“I am an idiot.” He blushed as he slotted between your legs, but you leaned in for a kiss, pushing him over to his back. 

“It’s your turn.” You smiled.

“It is?” 

“You tasted me, now I get to taste you.” You leaned in kissing him then moved down over his jaw line, nipping at his chin, slowly to the crease of his neck and shoulder where you sucked a huge mark. Moving down his torso, you puckered over his nipples as you teased his buds, hearing Dean moan lasciviously. Licking the sweat from his skin, you moved down his torso, slipping your fingers into the waistband of his boxer briefs, pulling them down and off. 

He was large, wide, purple, and leaking precome, you licked up the main vein and then teased the tip with your tongue before taking him in your mouth. “Fuck! Right there sweetheart.” Dean grunted. Before long and you had him all the way down your throat, sucking as he held your head, thrusting into your mouth. “Shit! I’m gonna cum right now. Fuck!” He came down your throat with a guttural moan. You licked around him, cleaning him up, then kissed up his body to his mouth, where he pulled you in for a deep kiss. “That was amazing.” 

Rolling you to your back, you cradled him between your hips and he looked at you. “I’ve missed you.”

“I’ve missed you too Dean.” You smiled.

“You know that for all these years I have cared about you.” Dean looked at you tenderly.

You were taken aback. You had always thought he possibly did, but was afraid to let you in and now he’s telling you that. 

His face was serious. “You mean more to me than just friends, so much more than lovers.”

You looked deep into his eyes as you felt him, already hard again and pressed against your entrance. “Yes Dean.”

He leaned in and kissed you tenderly, putting his weight on his elbows as he pushed himself in slowly, inch by inch, until you fully sheathed him. Letting you adjust, you exhaled. 

Kissing passionately, you moved your hips as he began to thrust.

“Oh God! Yes!” He was thrusting in you deeply, hitting your g-spot as his lips nibbled your neck and you bit into his shoulder. “I’m getting close Dean.”

“Me too, baby girl. Me too.” He thrusted faster and more erratic as you bucked against him. “Oh shit! I’m gonna cum.”

“Yes. Me too!” You felt your walls cave, squeezing him as his balls tightened and he released deep inside you. 

“Fuck baby. That was…”

“Incredible.” You smiled.

After a passionate kiss, Dean kissed down your torso and pressed his head against your abdomen. “I’m so glad I came.”

“I’m glad you did too.” You giggled. 

“Oh I came all right and I plan on doing it again and again if you want.” He smiled looking up at you. He moved up for a needy kiss as you rolled him over to his back and straddled his hips. “You will?”

“With you? Fuck yeah!”

You grabbed his cock that was at half mast and began stroking him, until he was hard again, then aligning him to your entrance, you sank down letting him impale you. He grabbed your thighs then hips in bruising grips while you ground your hips against him. “Fuck!” 

His hips met yours, sweat dampened your bodies, as you both grunted and groaned. “Dean!”

“I’m right here baby. I got you.” He dug his fingers into your thighs as you felt yourself getting closer. Raising himself, he held you, slipping his hand between your legs, putting pressure on your clit and you cried out, coming hard with a wail. Leaning in, you kissed him and he fell back to the bed; wrapped his arms around you, keeping him in you; as you rode out the waves. “I care about you Y/N.”

“I care about you too.” You smiled.

He let you go long enough to climb off him as you turned to your sides, then he pulled you close, holding you, and kissing your forehead. 

You laid that way for a while as you contemplated what you wanted to say. “So why come back to see me now after all these years?” 

“I wanted to see you.”

“And?”

Dean paused a minute. You looked at him until he spoke. “This might be the last time I see you.”

You pushed back against his chest and looked at him angry. “Wait. What? Why do you say that? After what we just did, you tell me now you can’t see me again.”

“It’s not like that Y/N.”

“What is it like then Dean? Enlighten me.”

He paused, deciding what he wanted to say. “It’s the end.”

“The end of what? us? Real classy Winchester. You fuck me, knowing how much I care for you, then say ‘it’s the end’. Dick move, Sir. Dick fucking move.”

“Of the world.” Dean said it angrily.

You looked at him confused. “What?”

“Chuck… I mean God said it’s the end of the world. Mom’s dead because of Jack. I was pissed, ready to get my revenge. Chuck wanted me to kill Jack. He was always holding the strings. He also considered Jack as a threat. I couldn’t do it. He’s just a kid.”

“Isn’t he the son of Lucifer?” You remembered the last time you spoke to Sam, he told you about Jack.”

“He’s a good kid. It took me a while to figure it out. I basically told Chuck to Fuck off, but Chuck didn’t like that, and killed Jack anyway. Sam took it hard and shot Chuck with Excalibur, the gun that could have killed him. We told Chuck we’re not his puppets anymore, so Chuck said , ‘welcome to the end,’ releasing all the evil sons of bitches we’ve already killed, we So either the world is ending or Sam, Jack, Cas, and I will probably die to save it.”

You were angry, but you could also see Dean was telling you the truth. “You really aren't just saying this to break it off with me, are you?”

Dean stared at you; his face turned angry. “Of course not. Y/N, I love you.”

You gasped. He never admitted those words to you before. “I’m telling you this so you wouldn’t think I just slept with you, then ghosted you, because that would be completely untrue.”

You looked at him as the tears rolled down your cheeks. “I love you too Dean. Geez, I have loved you forever, but now I have to sit here for the rest of my life or what little of it is left worrying that I’ll never see you again and you may be dead or if the world survives, did you make the ultimate sacrifice?”

“I know. I wasn’t planning on telling you any of this.” 

“What?” You were now both sad and pissed at him. 

“All I wanted to do was to see your face one last time and wish you ‘happy birthday’, but after seeing you, how beautiful you are, I wanted to stay and be with you. After last night and all this, I felt I needed to tell you the truth. I need you to know that I love you and wouldn’t want to leave you on purpose. Dammit! Sam warned me this would happen. He knew I cared for you more than just as friends, even when you lived with us. He knew we’d get too close if I came back to see you, but I don’t care anymore.” The lines of pain on his face made him look worn, even though he was still beautiful. Others would have just seen his beauty, but you saw every emotion on his face. 

The tears were streaming down your face as he pulled you to him, rubbing circles into the small of your back. “I want you to know Y/N that when I picture myself happy, it’s always with you.”

Your heart both lept and broke at his words. He pulled you closer in a bear hug as a single man tear fell down his cheek hearing your sobs. You were crying into his chest for the love you would be missing, the love you’ll never get to keep. He held you until you slowly fell asleep, then became the big spoon wrapping his arm around your waist as he drifted off to sleep. 

**Notes for the Chapter:**

> Thank you for reading. Kudos are always appreciated. Please don’t post this work in any forum or print without expressed written consent of the author.


	4. Sunday

Dean brought you brunch in bed Sunday early afternoon, bringing you fried eggs, bacon, toasted bagels, cheese, and two cups of coffee, so you made fried egg sandwiches with it, sat in bed, and ate with him. “This is so good. I was so hungry.” 

Dean smiled. “We worked up quite an appetite and I knew you would like this.”

“Even after all these years.”

“Of course. I remember more than you think. Remember, I cared a lot about you, but couldn’t tell you.”

“It is yummy.”

“You’re even yummier.” Dean smirked and you laughed.

After breakfast, you stayed in bed, curled up in Dean’s arms, and watched movies. 

“I haven’t done this in so long, sweetheart.”

“Feels good to lounge around and just relax.” You smiled. 

“Only with you.” Dean smiled. 

Three action movies six hours later, Dean grabbed the remote and stopped the movie as the final credits ran. “Stallone can kick Schwarzenegger’s ass.”

“I call Bullshit. Schwarzenegger’s the best. He can do comedy and action films, and he has some of the best one liners of them. ‘I’ll be back.’ ‘It’s not a tumor.’ Those are hilarious. Stallone just runs around yelling ‘Adrian’ everywhere.”

Dean laughed. “I guess you are right.”

You touched his chest. “I am right.”

Dean chuckled. “This has been great, spending time and watching movies with you, but I’d love to do something other than relaxing and watching movies right now.” Dean wiggled his eyebrows and clicked his tongue to the roof of his mouth.

“What do you have in mind?” You smirked.

Next thing you knew you were straddling Dean’s mouth as he lapped at your clit, two fingers deep inside you, sliding across your g spot as you gripped the headboard tight. “Shit! I’m gonna…”

“Cum for me baby.” As soon as he spoke the words, your back arched, seeing white, as the damn broke gushing on him. “Fuck. Fuck. Fuck. I’m sorry.” 

Dean lapped up your juices and helped you scoot down to his waist. “Damn Babe.”

“I’m so sorry.” You felt so embarrassed, your cheeks red, and not from the intense orgasm Dean just gave you. 

Dean chuckled. “Don’t be, babe. That just means I did my job correctly.”

“Oh boy did you.” You smiled. You leaned down kissing him passionately, then kissed down his body to reciprocate.

~~~~~~~~~~~~~

You awoke late at night to Dean’s deep snores; your heart broke to think of not seeing him again. 

You got up, padding to the bathroom and jumping into the shower. As the hot water scorched your skin, you whimpered; the heat was painful but a reminder that you were still alive. You heard his voice outside the shower. “Y/N. Taking a shower without me? Can I come in?”

“Yeah.” You turned down the hot water as he opened the curtain, stepping in, and stopping. You covered your breasts, nervous as his voice reflected anger. “Baby. What did you do to yourself?”

“Nothing.”

He noticed all the red heat marks up and down your body. “Why would you do this to yourself?”

As you kept your body turned away from him, you cried. “I just wanted a reminder that these last few days with you were real.”

“Baby. This is real.” He turned you around leaned in, kissing your neck and shoulders first. “I’m real.” His lips trailed down your skin as his lips puckered over a nipple, and he licked, bit and sucked your peak until it was hard. “This is real, you are real, and really beautiful.” He moved down your torso, kissing all the red spots, which covered most of your body.

Moans and whimpers filled the shower as Dean was on his knees with one of your legs over his shoulder, eating you out while you pressed the shower wall with one arm, your other hand gripped Dean’s hair while you rode his 

mouth with his tongue buried deep inside your entrance. “Oh fuck Dean. Please! Please! Please!” You whimpered as you were getting close. He urged you on as his thumb put pressure on your clit, and you let out a squeal when you came. “Oh God Yes! Yes! Yes!”

Dean continued lapping at your pussy lips putting pressure on your clit until you pushed his head away, oversensitized by his touch.

“Shit! I can’t. “No more.” You were panting.

“Sorry Babe.” Dean pulled away chuckling. He moved up and kissed you, as he hooked your thighs, lifting you up, giving you time to wrap your legs around his waist, your arms around his neck as he pushed you down on his cock. You gripped his biceps, digging into his shoulders as he came hard; causing your orgasm; you both were crying out each other’s names. You took your time after washing each other’s bodies, spending more time making out and groping each other than cleaning, but it felt amazingly tender the way you cared for each other. After the amazing shower, he carried you back to bed, holding you close. 

**Notes for the Chapter:**

> Thank you for reading. Kudos are appreciated. Please do not post this in any forum or print without express written consent of the author.

**Author's Note:**

> Thank you for reading. Kudos are appreciated. Please do not post this work in any forum or in media without express written consent by author.


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